About Me
Brett Chereskin
I flew Army reconnaissance planes for 12 years, then moved to fintech. Now I run operations at dub, invest in veteran founders, build things with AI, and write about the intersection of all of it.
Experience
Career Journey
COO & Board Member at dub
New York City
I partner with the CEO to operate the business — sitting on the board of directors and running customer operations, brokerage operations, finance, HR, and most G&A functions at a social investing platform. Many of those I handle single-handedly, powered by AI, operating at the scale of a much larger team. It's the proving ground for everything I write about — using AI to do real operational work, not just talk about it.
Business Operations at Affirm
San Francisco Bay Area
Ran business operations at one of the largest BNPL companies during its hypergrowth phase. Built operational infrastructure that scales under regulatory pressure — compliance, risk, and cross-functional ops. Learned how fast-growing fintechs break and what it takes to hold them together when the stakes are real.
U.S. Army Officer
Fixed-Wing & Rotary-Wing Aviator · UAS Commander · 160th SOAR
12 years as an Army officer and aviator. Started in fixed-wing reconnaissance, commanded a UAS (drone) unit on the conventional side, then joined the 160th Special Operations Aviation Regiment where I helped build their first organic large UAS unit from scratch. The leadership, discipline, and mission planning from the military is the foundation that makes everything else work.
Background
Education & Credentials
West Point
United States Military Academy · Class of 2006
Four-year undergraduate program combining rigorous academics with military leadership training.
Licenses & Certifications
- Commercial Pilot — Fixed Wing & Rotary (FAA)
- Commercial UAS Certificate (FAA Part 107)
- Series 99 — Operations Professional (FINRA)
- Securities Industry Essentials (FINRA)
Advisory & Investing
Where I Put My Time & Capital
Advisory
Grady AI
AI-powered grading platform for higher education
Stage 2 Capital
Catalyst LP — GTM-focused fund, active with portfolio companies
Military → Civilian
Helping veterans transition into the startup ecosystem
Investing
A fund investing specifically in military founders. I believe the leadership training, risk calibration, and mission orientation that veterans bring to startups is a genuine competitive advantage.
B2B go-to-market focused fund. As a Catalyst LP, I actively help portfolio companies with operational strategy and scaling.
TruvAngel Investment
Consumer-permissioned financial data platform powering income and employment verification for lenders.
Media
Podcasts & Conversations
Beyond Work
Life Outside Work
I've been married to my wife Lisa for over 13 years — we met when I was stationed in Germany and still go back as often as we can. We don't have human kids, but our Pomsky Tanuki is the best city dog you'll ever meet. Most of our favorite NYC spots we discovered walking him through different neighborhoods.
Born and raised on Long Island. After 15 years traveling the world with the military and doing the startup thing in San Francisco, I finally came back to the city — and we've been making up for lost time. We love food, wine, and Broadway.
See our NYC favorites